Hydrochloric Acid → HCID 21029525, compound

HRID 2364821Notes

Reaction equation

HRID 2364821 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([OH:13])[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].O.[OH-].[Li+].Cl>ClCCl.CN(C=O)C.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([O:13][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])[CH2:10][C@H:9]1[C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 168937Lithium hydroxide, monohydrateHCID 688614(2S,4S)-1-(tert-butoxycarbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 21029525HCID 21029525, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolvent3×HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 81A (5.31, 22.96 mmol) and imidazole (7.82 g, 115 mmol) in dichloromethane (106 mL) and DMF (21.3 mL) was added tert-butyldimethylsilyl chloride (7.61 g, 50.5 mmol) and the mixture stirred at room temperature overnight. The mixture then had water (425 mL) added and the solution was extracted with EtOAc and the organic extract concentrated to a residue that was dissolved in 25% EtOAc and 75% hexanes then extracted with brine and the organic extract concentrated to a solid. The resultant solid was dissolved in methanol (65 mL) and water (85 mL) then lithium hydroxide monohydrate (1.93 g, 46 mmol) added and the solution stirred at room temperature for 2 h. Afterwards water (106 mL) and a solution of 1N aqueous hydrochloric acid was added until a pH of 2 was reached. The mixture was then extracted with a mixture of 25% EtOAc and 75% hexanes, the organic extract dried, filtered and concentrated to a colorless solid. MS (ESI) m/z 346 (M+H)+.

Workup

  1. additionadded
  2. extractionthe solution was extracted with EtOAc
  3. extractionthe organic extract
  4. concentrationconcentrated to a residue that
  5. dissolutionwas dissolved in 25% EtOAc
  6. extraction75% hexanes then extracted with brine
  7. extractionthe organic extract
  8. concentrationconcentrated to a solid
  9. dissolutionThe resultant solid was dissolved in methanol (65 mL)
  10. stirringthe solution stirred at room temperature for 2 h
  11. extractionThe mixture was then extracted with a mixture of 25% EtOAc and 75% hexanes
  12. extractionthe organic extract
  13. customdried
  14. filtrationfiltered
  15. concentrationconcentrated to a colorless solid

Sources & evidence

ORD record
ord-f3d408054a78453993214b8dd30bb011
Source dataset
uspto-grants-2014_04
Patent number
US08691938B2

Reaction notes

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